Methanesulfonyl azide

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Methanesulfonyl azide
Mesyl azide.svg
Names
Other names
Mesyl azide
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/CH3N3O2S/c1-7(5,6)4-3-2/h1H3
    Key: BHQIGUWUNPQBJY-UHFFFAOYSA-N
  • CS(=O)(=O)N=[N+]=[N-]
Properties
CH3N3O2S
Molar mass 121.12 g·mol −1
Melting point 18 °C (64 °F; 291 K)
Boiling point 120 °C (248 °F; 393 K) decomposes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methanesulfonyl azide is the azide of methanesulfonic acid. It is used as a reagent for the production of diazo compounds.

Contents

Preparation

Methanesulfonyl azide can be prepared from methanesulfonyl chloride by reaction with sodium azide in ethanol [1] or methanol, [2] Preparation in situ is also possible, for example in acetonitrile, and is advantageous to avoid explosion hazards. [3]

Properties

Methanesulfonyl azide melts at 18 °C and decomposes from 120 °C. [1] Like many other azides, it is explosive. [3] At low temperature, methanesulfonyl azide crystallizes in the triclinic crystal system in the space group P1 with the lattice parameters a = 5.6240 Å; b = 5.9498 Å, c = 7.6329 Å, α = 72.216°, β = 70.897°, and γ = 88.601°, and two molecules per unit cell. [1]

Mesyl azide is an antidote for hydrogen sulfide poisoning in mice. [4]

Reactions

Methanesulfonyl azide is part of the sulfonyl azides, a family of reagents for diazo transfer. Within the family, methanesulfonyl azide has particularly simple, inexpensive production and a straightforward purification of the reaction mixture. [2]

The photolysis of methanesulfonyl azide in a matrix of argon or neon yields a short-lived nitrene. [1] If methanesulfonyl azide is irradiated in the presence of a hydrocarbon, methanesulfonyl amide is formed, as well as N-substituted derivatives by reaction with the hydrocarbon. [5]

References

  1. 1 2 3 4 Deng, Guohai; Li, Dingqing; Wu, Zhuang; Li, Hongmin; Bernhardt, Eduard; Zeng, Xiaoqing (2016-07-21), "Methanesulfonyl Azide: Molecular Structure and Photolysis in Solid Noble Gas Matrices", The Journal of Physical Chemistry A, vol. 120, no. 28, pp. 5590–5597, Bibcode:2016JPCA..120.5590D, doi:10.1021/acs.jpca.6b05533, PMID   27383463
  2. 1 2 Taber, Douglass F.; Ruckle, Robert E.; Hennessy, Michael J. (October 1986), "Mesyl azide: a superior reagent for diazo transfer", The Journal of Organic Chemistry, vol. 51, no. 21, pp. 4077–4078, doi:10.1021/jo00371a034
  3. 1 2 Lynch, Denis; O’Mahony, Rosella M.; McCarthy, Daniel G.; Bateman, Lorraine M.; Collins, Stuart G.; Maguire, Anita R. (2019-06-16), "Mechanistic Study of In Situ Generation and Use of Methanesulfonyl Azide as a Diazo Transfer Reagent with Real-Time Monitoring by FlowNMR", European Journal of Organic Chemistry, vol. 2019, no. 22, pp. 3575–3580, doi:10.1002/ejoc.201900184, hdl: 10468/8205
  4. ↑ Howes, Laura (25 June 2019). "Data mining for a hydrogen sulfide antidote" . Chemical and Engineering News. Vol. 97, no. 26. American Chemical Society. ISSN   0009-2347.
  5. ↑ Torimoto, Noboru; Shingaki, Tadao; Nagai, Toshikazu (February 1978), "Sensitized photolyses of methanesulfonyl azide in hydrocarbons", The Journal of Organic Chemistry, vol. 43, no. 4, pp. 631–633, doi:10.1021/jo00398a023
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